# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GP_75NP
_database_code_depnum_ccdc_archive 'CCDC 2087800'
loop_
_audit_author_name
_audit_author_address
'Jen-Chieh Hsieh'
;Tamkang University
Taiwan
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Br0 N O'
_chemical_formula_weight         311.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3912(2)
_cell_length_b                   9.6810(3)
_cell_length_c                   10.9201(3)
_cell_angle_alpha                69.3430(10)
_cell_angle_beta                 66.3600(10)
_cell_angle_gamma                67.4890(10)
_cell_volume                     816.58(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    128
_cell_measurement_theta_min      2.0922
_cell_measurement_theta_max      20.5389

_exptl_crystal_description       lamellar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7128
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 QUEST CMOS PHOTON II four-circle KAPPA diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32840
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.343
_diffrn_reflns_theta_max         28.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3957
_reflns_number_gt                2345
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.2164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3957
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2218(2) 0.2780(2) 0.85843(15) 0.0761(5) Uani 1 1 d . . . . .
N1 N 0.28363(18) 0.30679(18) 0.62874(16) 0.0484(4) Uani 1 1 d . . . . .
C1 C 0.5520(3) 0.1626(3) 0.8465(2) 0.0632(6) Uani 1 1 d . . . . .
H1 H 0.476053 0.167083 0.932787 0.076 Uiso 1 1 calc R U . . .
C2 C 0.7134(3) 0.1113(3) 0.8332(2) 0.0713(7) Uani 1 1 d . . . . .
H2 H 0.746815 0.081143 0.910550 0.086 Uiso 1 1 calc R U . . .
C3 C 0.8270(3) 0.1039(3) 0.7060(2) 0.0651(6) Uani 1 1 d . . . . .
H3 H 0.936673 0.069551 0.697988 0.078 Uiso 1 1 calc R U . . .
C4 C 0.7800(3) 0.1467(2) 0.5910(2) 0.0539(5) Uani 1 1 d . . . . .
H4 H 0.858121 0.140751 0.505807 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6148(2) 0.1996(2) 0.60051(18) 0.0427(4) Uani 1 1 d . . . . .
C6 C 0.4998(2) 0.2087(2) 0.73031(19) 0.0475(5) Uani 1 1 d . . . . .
C7 C 0.3274(3) 0.2647(2) 0.7472(2) 0.0521(5) Uani 1 1 d . . . . .
C8 C 0.1100(2) 0.3717(3) 0.6443(3) 0.0738(7) Uani 1 1 d . . . . .
H8A H 0.094036 0.457513 0.568192 0.111 Uiso 1 1 calc R U . . .
H8B H 0.054477 0.405415 0.728554 0.111 Uiso 1 1 calc R U . . .
H8C H 0.067883 0.294517 0.646445 0.111 Uiso 1 1 calc R U . . .
C9 C 0.3972(2) 0.2917(2) 0.50019(18) 0.0412(4) Uani 1 1 d . . . . .
C10 C 0.5584(2) 0.2405(2) 0.48367(17) 0.0403(4) Uani 1 1 d . . . . .
C11 C 0.3370(2) 0.3325(2) 0.38133(19) 0.0429(4) Uani 1 1 d . . . . .
C12 C 0.2720(3) 0.2351(2) 0.3660(2) 0.0581(6) Uani 1 1 d . . . . .
H12 H 0.254140 0.148657 0.435836 0.070 Uiso 1 1 calc R U . . .
C13 C 0.2338(3) 0.2659(3) 0.2476(3) 0.0691(7) Uani 1 1 d . . . . .
H13 H 0.191089 0.199495 0.237967 0.083 Uiso 1 1 calc R U . . .
C14 C 0.2582(3) 0.3935(3) 0.1444(2) 0.0649(6) Uani 1 1 d . . . . .
H14 H 0.233764 0.412813 0.064326 0.078 Uiso 1 1 calc R U . . .
C15 C 0.3188(3) 0.4924(3) 0.1598(2) 0.0619(6) Uani 1 1 d . . . . .
H15 H 0.333454 0.580375 0.090830 0.074 Uiso 1 1 calc R U . . .
C16 C 0.3581(2) 0.4616(2) 0.2778(2) 0.0537(5) Uani 1 1 d . . . . .
H16 H 0.399538 0.529173 0.287385 0.064 Uiso 1 1 calc R U . . .
C17 C 0.6771(2) 0.2195(2) 0.34655(18) 0.0405(4) Uani 1 1 d . . . . .
C18 C 0.6903(2) 0.1033(2) 0.29358(19) 0.0460(4) Uani 1 1 d . . . . .
H18 H 0.626037 0.036710 0.344865 0.055 Uiso 1 1 calc R U . . .
C19 C 0.7972(3) 0.0844(3) 0.1659(2) 0.0585(6) Uani 1 1 d . . . . .
H19 H 0.803699 0.006263 0.131475 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8938(3) 0.1805(3) 0.0896(2) 0.0654(6) Uani 1 1 d . . . . .
H20 H 0.965442 0.167971 0.003367 0.079 Uiso 1 1 calc R U . . .
C21 C 0.8846(3) 0.2954(3) 0.1409(2) 0.0634(6) Uani 1 1 d . . . . .
H21 H 0.950893 0.360097 0.089647 0.076 Uiso 1 1 calc R U . . .
C22 C 0.7763(2) 0.3151(2) 0.2693(2) 0.0536(5) Uani 1 1 d . . . . .
H22 H 0.770519 0.393101 0.303512 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.234(2) . ?
N1 C7 1.391(2) . ?
N1 C9 1.398(2) . ?
N1 C8 1.466(3) . ?
C1 C2 1.365(3) . ?
C1 C6 1.407(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(3) . ?
C5 C10 1.446(2) . ?
C6 C7 1.452(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.356(2) . ?
C9 C11 1.489(2) . ?
C10 C17 1.493(2) . ?
C11 C16 1.376(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.382(2) . ?
C17 C22 1.384(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C9 122.69(16) . . ?
C7 N1 C8 116.45(17) . . ?
C9 N1 C8 120.85(16) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.29(17) . . ?
C6 C5 C10 118.66(17) . . ?
C4 C5 C10 123.02(17) . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 121.18(17) . . ?
C1 C6 C7 119.20(19) . . ?
O1 C7 N1 119.9(2) . . ?
O1 C7 C6 123.65(19) . . ?
N1 C7 C6 116.43(17) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 121.08(16) . . ?
C10 C9 C11 120.56(16) . . ?
N1 C9 C11 118.36(15) . . ?
C9 C10 C5 119.85(16) . . ?
C9 C10 C17 120.09(15) . . ?
C5 C10 C17 120.00(16) . . ?
C16 C11 C12 118.49(18) . . ?
C16 C11 C9 120.19(16) . . ?
C12 C11 C9 121.07(17) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.97(19) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C22 118.31(18) . . ?
C18 C17 C10 120.42(16) . . ?
C22 C17 C10 121.26(17) . . ?
C19 C18 C17 121.04(19) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.5(2) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2087808'
loop_
_audit_author_name
_audit_author_address
'Jen-Chieh Hsieh'
;Tamkang University
Taiwan
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         313.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0230(3)
_cell_length_b                   7.74160(10)
_cell_length_c                   19.2617(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.8500(10)
_cell_angle_gamma                90
_cell_volume                     1740.70(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    283
_cell_measurement_theta_min      1.7445
_cell_measurement_theta_max      22.4281

_exptl_crystal_description       lamellar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.152
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_correction_T_min  0.7231
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 QUEST CMOS PHOTON II four-circle KAPPA diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28519
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4302
_reflns_number_gt                3020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.4495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4302
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73376(8) 0.57907(12) 0.56908(5) 0.0423(2) Uani 1 1 d . . . . .
N1 N 0.81973(13) 0.52899(18) 0.68917(7) 0.0574(4) Uani 1 1 d . . . . .
C1 C 0.80674(12) 0.61930(18) 0.63363(7) 0.0411(3) Uani 1 1 d . . . . .
C2 C 0.86486(12) 0.78116(18) 0.62544(7) 0.0392(3) Uani 1 1 d . . . . .
C3 C 0.94875(13) 0.8711(2) 0.67385(8) 0.0483(4) Uani 1 1 d . . . . .
H3 H 0.976425 0.831067 0.720307 0.058 Uiso 1 1 calc R U . . .
C4 C 0.98994(14) 1.0218(2) 0.65103(9) 0.0545(4) Uani 1 1 d . . . . .
H4 H 1.046761 1.083852 0.682380 0.065 Uiso 1 1 calc R U . . .
C5 C 0.94767(14) 1.0817(2) 0.58200(9) 0.0546(4) Uani 1 1 d . . . . .
H5 H 0.976457 1.183652 0.567690 0.066 Uiso 1 1 calc R U . . .
C6 C 0.86330(13) 0.99222(19) 0.53395(8) 0.0484(4) Uani 1 1 d . . . . .
H6 H 0.834783 1.032982 0.487690 0.058 Uiso 1 1 calc R U . . .
C7 C 0.82254(12) 0.84039(17) 0.55669(7) 0.0383(3) Uani 1 1 d . . . . .
C8 C 0.7511(2) 0.3719(2) 0.68496(11) 0.0787(6) Uani 1 1 d . . . . .
H8A H 0.673057 0.396863 0.661284 0.118 Uiso 1 1 calc R U . . .
H8B H 0.754481 0.330050 0.732339 0.118 Uiso 1 1 calc R U . . .
H8C H 0.780775 0.285436 0.658495 0.118 Uiso 1 1 calc R U . . .
C9 C 0.73299(12) 0.71604(17) 0.51676(7) 0.0388(3) Uani 1 1 d . . . . .
C10 C 0.76857(12) 0.63837(18) 0.45275(7) 0.0423(3) Uani 1 1 d . . . . .
C11 C 0.83830(15) 0.4947(2) 0.46146(9) 0.0587(4) Uani 1 1 d . . . . .
H11 H 0.859547 0.441607 0.505991 0.070 Uiso 1 1 calc R U . . .
C12 C 0.87706(18) 0.4284(3) 0.40484(11) 0.0740(6) Uani 1 1 d . . . . .
H12 H 0.923922 0.331259 0.411671 0.089 Uiso 1 1 calc R U . . .
C13 C 0.84724(17) 0.5041(3) 0.33921(10) 0.0699(5) Uani 1 1 d . . . . .
H13 H 0.873567 0.459068 0.301330 0.084 Uiso 1 1 calc R U . . .
C14 C 0.77826(17) 0.6470(3) 0.32937(9) 0.0680(5) Uani 1 1 d . . . . .
H14 H 0.757871 0.699369 0.284653 0.082 Uiso 1 1 calc R U . . .
C15 C 0.73836(15) 0.7146(2) 0.38599(8) 0.0574(4) Uani 1 1 d . . . . .
H15 H 0.691205 0.811449 0.378808 0.069 Uiso 1 1 calc R U . . .
C16 C 0.61164(12) 0.7937(2) 0.49768(8) 0.0474(4) Uani 1 1 d . . . . .
H16A H 0.613413 0.901549 0.472318 0.057 Uiso 1 1 calc R U . . .
H16B H 0.560967 0.715332 0.465601 0.057 Uiso 1 1 calc R U . . .
C17 C 0.56330(13) 0.8273(2) 0.56164(8) 0.0470(4) Uani 1 1 d . . . . .
C18 C 0.47845(16) 0.7227(3) 0.57554(12) 0.0745(6) Uani 1 1 d . . . . .
H18 H 0.450035 0.632484 0.544479 0.089 Uiso 1 1 calc R U . . .
C19 C 0.4350(2) 0.7495(3) 0.63472(14) 0.0954(7) Uani 1 1 d . . . . .
H19 H 0.378014 0.677192 0.643358 0.115 Uiso 1 1 calc R U . . .
C20 C 0.47533(19) 0.8822(3) 0.68078(12) 0.0842(6) Uani 1 1 d . . . . .
H20 H 0.446281 0.899962 0.720836 0.101 Uiso 1 1 calc R U . . .
C21 C 0.55855(16) 0.9885(3) 0.66755(10) 0.0662(5) Uani 1 1 d . . . . .
H21 H 0.586249 1.078937 0.698687 0.079 Uiso 1 1 calc R U . . .
C22 C 0.60165(14) 0.9622(2) 0.60821(8) 0.0525(4) Uani 1 1 d . . . . .
H22 H 0.657461 1.036529 0.599360 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3749(16) . ?
O1 C9 1.4615(16) . ?
N1 C1 1.2559(18) . ?
N1 C8 1.461(2) . ?
C1 C2 1.462(2) . ?
C2 C7 1.3785(18) . ?
C2 C3 1.386(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(2) . ?
C6 H6 0.9300 . ?
C7 C9 1.5102(19) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.5221(19) . ?
C9 C16 1.5391(19) . ?
C10 C11 1.379(2) . ?
C10 C15 1.382(2) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.505(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.378(2) . ?
C17 C22 1.382(2) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 110.89(10) . . ?
C1 N1 C8 117.56(15) . . ?
N1 C1 O1 124.51(14) . . ?
N1 C1 C2 127.16(14) . . ?
O1 C1 C2 108.33(11) . . ?
C7 C2 C3 121.40(14) . . ?
C7 C2 C1 108.24(12) . . ?
C3 C2 C1 130.36(13) . . ?
C4 C3 C2 117.98(14) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 120.78(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.08(15) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.14(14) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C2 C7 C6 120.61(13) . . ?
C2 C7 C9 109.35(12) . . ?
C6 C7 C9 130.04(13) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C7 103.01(10) . . ?
O1 C9 C10 108.38(11) . . ?
C7 C9 C10 111.10(11) . . ?
O1 C9 C16 107.30(11) . . ?
C7 C9 C16 113.08(11) . . ?
C10 C9 C16 113.27(11) . . ?
C11 C10 C15 118.32(14) . . ?
C11 C10 C9 120.05(13) . . ?
C15 C10 C9 121.51(14) . . ?
C10 C11 C12 120.88(17) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.59(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.54(16) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.37(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.30(17) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C9 113.69(12) . . ?
C17 C16 H16A 108.8 . . ?
C9 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C9 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C22 117.74(15) . . ?
C18 C17 C16 120.42(15) . . ?
C22 C17 C16 121.84(14) . . ?
C17 C18 C19 121.13(19) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.55(19) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.23(18) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.10(16) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02_a
_database_code_depnum_ccdc_archive 'CCDC 2089397'
loop_
_audit_author_name
_audit_author_address
'Jen-Chieh Hsieh'
;Tamkang University
Taiwan
;
_audit_update_record             
;
2021-06-11 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8118(4)
_cell_length_b                   18.3413(8)
_cell_length_c                   10.4793(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.612(2)
_cell_angle_gamma                90
_cell_volume                     1652.80(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.214
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_correction_T_min  0.7199
_exptl_absorpt_correction_T_max  0.7379
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 QUEST CMOS PHOTON II four-circle KAPPA diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25049
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4104
_reflns_number_gt                3157
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+0.6078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4104
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69623(14) 0.34432(7) 0.54117(11) 0.0508(3) Uani 1 1 d . . . . .
N1 N 0.77440(19) 0.31347(9) 0.35384(15) 0.0558(4) Uani 1 1 d . . . . .
C1 C 0.9260(2) 0.29689(14) 0.4365(2) 0.0672(6) Uani 1 1 d . . . . .
H1A H 0.9992 0.2878 0.3827 0.101 Uiso 1 1 calc R U . . .
H1B H 0.9179 0.2545 0.4882 0.101 Uiso 1 1 calc R U . . .
H1C H 0.9608 0.3375 0.4931 0.101 Uiso 1 1 calc R U . . .
C2 C 0.6671(2) 0.33626(10) 0.40754(16) 0.0454(4) Uani 1 1 d . . . . .
C3 C 0.5124(2) 0.35639(9) 0.33470(16) 0.0466(4) Uani 1 1 d . . . . .
C4 C 0.4768(2) 0.35097(12) 0.19853(18) 0.0585(5) Uani 1 1 d . . . . .
H4 H 0.5518 0.3345 0.1552 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3325(3) 0.36977(14) 0.1285(2) 0.0692(6) Uani 1 1 d . . . . .
H5 H 0.3098 0.3661 0.0378 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2204(2) 0.39418(14) 0.1917(2) 0.0667(6) Uani 1 1 d . . . . .
H6 H 0.1223 0.4068 0.1436 0.080 Uiso 1 1 calc R U . . .
C7 C 0.2536(2) 0.39994(12) 0.3267(2) 0.0580(5) Uani 1 1 d . . . . .
H7 H 0.1771 0.4166 0.3682 0.070 Uiso 1 1 calc R U . . .
C8 C 0.39925(19) 0.38129(9) 0.40140(16) 0.0441(4) Uani 1 1 d . . . . .
C9 C 0.43957(18) 0.38527(9) 0.54401(15) 0.0415(3) Uani 1 1 d . . . . .
C10 C 0.58508(18) 0.36776(9) 0.60693(15) 0.0409(3) Uani 1 1 d . . . . .
C11 C 0.65194(18) 0.36992(9) 0.74940(15) 0.0420(4) Uani 1 1 d . . . . .
C12 C 0.6230(2) 0.42769(11) 0.82630(19) 0.0556(5) Uani 1 1 d . . . . .
H12 H 0.5594 0.4659 0.7885 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6882(3) 0.42866(14) 0.9590(2) 0.0673(6) Uani 1 1 d . . . . .
H13 H 0.6679 0.4674 1.0100 0.081 Uiso 1 1 calc R U . . .
C14 C 0.7830(2) 0.37251(14) 1.01594(19) 0.0638(5) Uani 1 1 d . . . . .
H14 H 0.8254 0.3730 1.1054 0.077 Uiso 1 1 calc R U . . .
C15 C 0.8146(3) 0.31579(13) 0.94053(19) 0.0631(5) Uani 1 1 d . . . . .
H15 H 0.8795 0.2781 0.9788 0.076 Uiso 1 1 calc R U . . .
C16 C 0.7505(2) 0.31436(11) 0.80815(18) 0.0531(4) Uani 1 1 d . . . . .
H16 H 0.7734 0.2759 0.7576 0.064 Uiso 1 1 calc R U . . .
C17 C 0.31737(18) 0.40439(9) 0.61727(16) 0.0431(4) Uani 1 1 d . . . . .
C18 C 0.2531(2) 0.47366(11) 0.6099(2) 0.0582(5) Uani 1 1 d . . . . .
H18 H 0.2867 0.5092 0.5590 0.070 Uiso 1 1 calc R U . . .
C19 C 0.1393(3) 0.49038(13) 0.6778(2) 0.0707(6) Uani 1 1 d . . . . .
H19 H 0.0982 0.5372 0.6735 0.085 Uiso 1 1 calc R U . . .
C20 C 0.0866(2) 0.43800(15) 0.7517(2) 0.0698(6) Uani 1 1 d . . . . .
H20 H 0.0098 0.4493 0.7969 0.084 Uiso 1 1 calc R U . . .
C21 C 0.1483(2) 0.36888(13) 0.7583(2) 0.0611(5) Uani 1 1 d . . . . .
H21 H 0.1124 0.3333 0.8077 0.073 Uiso 1 1 calc R U . . .
C22 C 0.2634(2) 0.35191(10) 0.69193(17) 0.0491(4) Uani 1 1 d . . . . .
H22 H 0.3049 0.3051 0.6974 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.375(2) . ?
O1 C10 1.3835(19) . ?
N1 C2 1.272(2) . ?
N1 C1 1.457(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.457(3) . ?
C3 C4 1.396(2) . ?
C3 C8 1.413(2) . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.460(2) . ?
C9 C10 1.346(2) . ?
C9 C17 1.494(2) . ?
C10 C11 1.481(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.392(2) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 C22 1.388(2) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C10 123.06(13) . . ?
C2 N1 C1 118.63(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 O1 119.62(16) . . ?
N1 C2 C3 123.53(16) . . ?
O1 C2 C3 116.84(14) . . ?
C4 C3 C8 120.23(17) . . ?
C4 C3 C2 119.55(16) . . ?
C8 C3 C2 120.23(15) . . ?
C5 C4 C3 120.40(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.26(19) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.17(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 121.25(19) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 117.69(16) . . ?
C7 C8 C9 123.48(16) . . ?
C3 C8 C9 118.83(15) . . ?
C10 C9 C8 118.82(15) . . ?
C10 C9 C17 121.36(14) . . ?
C8 C9 C17 119.73(14) . . ?
C9 C10 O1 122.16(14) . . ?
C9 C10 C11 127.88(14) . . ?
O1 C10 C11 109.96(13) . . ?
C12 C11 C16 118.55(16) . . ?
C12 C11 C10 121.50(16) . . ?
C16 C11 C10 119.91(15) . . ?
C13 C12 C11 120.30(19) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.35(19) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.86(18) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.64(18) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C18 C17 C22 118.75(16) . . ?
C18 C17 C9 121.18(16) . . ?
C22 C17 C9 120.05(15) . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.56(19) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.4(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.39(18) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d23470
_database_code_depnum_ccdc_archive 'CCDC 2109230'
loop_
_audit_author_name
_audit_author_address
'Jen-Chieh Hsieh'
;Tamkang University
Taiwan
;
_audit_update_record             
;
2021-09-11 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 N O Si'
_chemical_formula_sum            'C19 H23 N O Si'
_chemical_formula_weight         309.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.156(3)
_cell_length_b                   13.973(3)
_cell_length_c                   21.035(5)
_cell_angle_alpha                101.448(7)
_cell_angle_beta                 95.499(8)
_cell_angle_gamma                110.186(6)
_cell_volume                     2702.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4186
_cell_measurement_theta_min      2.223
_cell_measurement_theta_max      23.151

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9337
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi scan & omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            56021
_diffrn_reflns_av_R_equivalents  0.2132
_diffrn_reflns_av_sigmaI/netI    0.1958
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.11
_reflns_number_total             9592
_reflns_number_gt                5359
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9592
_refine_ls_number_parameters     201
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.3061
_refine_ls_R_factor_gt           0.2415
_refine_ls_wR_factor_ref         0.5518
_refine_ls_wR_factor_gt          0.5306
_refine_ls_goodness_of_fit_ref   1.686
_refine_ls_restrained_S_all      1.685
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1755(13) 0.0422(10) 0.0855(6) 0.044(3) Uiso 1 1 d . . .
H1A H 0.0835 0.0319 0.0601 0.066 Uiso 1 1 calc R . .
H1B H 0.1907 -0.0245 0.0771 0.066 Uiso 1 1 calc R . .
H1C H 0.2521 0.0953 0.0721 0.066 Uiso 1 1 calc R . .
C2 C 0.3449(13) 0.1071(10) 0.2211(6) 0.045(3) Uiso 1 1 d . . .
H2A H 0.4213 0.1583 0.2064 0.068 Uiso 1 1 calc R . .
H2B H 0.3591 0.0402 0.2144 0.068 Uiso 1 1 calc R . .
H2C H 0.3466 0.1339 0.2680 0.068 Uiso 1 1 calc R . .
C3 C 0.164(2) 0.2263(15) 0.1890(9) 0.097(6) Uiso 1 1 d . . .
H3A H 0.0735 0.2206 0.1646 0.146 Uiso 1 1 calc R . .
H3B H 0.2433 0.2737 0.1735 0.146 Uiso 1 1 calc R . .
H3C H 0.1696 0.2544 0.2361 0.146 Uiso 1 1 calc R . .
C4 C 0.0371(10) -0.0111(7) 0.2055(5) 0.023(2) Uiso 1 1 d . . .
C5 C -0.0920(10) -0.0107(7) 0.2161(5) 0.023(2) Uiso 1 1 d . . .
H5 H -0.1422 -0.0567 0.2409 0.027 Uiso 1 1 calc R . .
C6 C -0.1602(10) 0.0556(7) 0.1920(4) 0.019(2) Uiso 1 1 d D . .
C7 C -0.1870(14) 0.0386(10) 0.1215(6) 0.050(3) Uiso 1 1 d D . .
H7 H -0.1620 -0.0100 0.0915 0.059 Uiso 1 1 calc R . .
C8 C -0.2613(14) 0.1093(10) 0.1012(7) 0.056(4) Uiso 1 1 d D . .
H8 H -0.2873 0.1076 0.0563 0.068 Uiso 1 1 calc R . .
C9 C -0.2891(13) 0.1776(10) 0.1532(7) 0.056(4) Uiso 1 1 d D . .
H9 H -0.3353 0.2207 0.1396 0.067 Uiso 1 1 calc R . .
C10 C -0.2615(10) 0.1895(8) 0.2150(5) 0.028(2) Uiso 1 1 d D . .
H10 H -0.2807 0.2403 0.2460 0.034 Uiso 1 1 calc R . .
C11 C -0.2006(14) 0.1216(10) 0.2335(7) 0.052(3) Uiso 1 1 d D . .
H11 H -0.1867 0.1221 0.2789 0.063 Uiso 1 1 calc R . .
C12 C 0.0817(12) -0.0929(8) 0.2328(5) 0.034(3) Uiso 1 1 d D . .
C13 C 0.1128(14) -0.0773(11) 0.3019(7) 0.056(4) Uiso 1 1 d D . .
H13 H 0.1092 -0.0159 0.3294 0.067 Uiso 1 1 calc R . .
C14 C 0.1483(14) -0.1473(11) 0.3311(7) 0.062(4) Uiso 1 1 d D . .
H14 H 0.1488 -0.1397 0.3770 0.075 Uiso 1 1 calc R . .
C15 C 0.1800(12) -0.2206(10) 0.3002(6) 0.047(3) Uiso 1 1 d D . .
H15 H 0.2107 -0.2649 0.3217 0.057 Uiso 1 1 calc R . .
C16 C 0.1664(11) -0.2329(8) 0.2299(5) 0.032(3) Uiso 1 1 d D . .
H16 H 0.1899 -0.2871 0.2046 0.039 Uiso 1 1 calc R . .
C17 C 0.1202(9) -0.1686(7) 0.1966(4) 0.0150(19) Uiso 1 1 d D . .
C18 C 0.0927(11) -0.2015(8) 0.1224(5) 0.028(2) Uiso 1 1 d . . .
C19 C -0.0694(12) -0.2305(8) 0.0172(5) 0.032(3) Uiso 1 1 d . . .
H19A H -0.1634 -0.2281 0.0044 0.048 Uiso 1 1 calc R . .
H19B H -0.0717 -0.3014 -0.0010 0.048 Uiso 1 1 calc R . .
H19C H 0.0021 -0.1795 0.0000 0.048 Uiso 1 1 calc R . .
C20 C 0.343(2) 0.5291(15) 0.2009(9) 0.092(6) Uiso 1 1 d . . .
H20A H 0.3360 0.5984 0.2062 0.137 Uiso 1 1 calc R . .
H20B H 0.3687 0.5184 0.2443 0.137 Uiso 1 1 calc R . .
H20C H 0.2508 0.4743 0.1786 0.137 Uiso 1 1 calc R . .
C21 C 0.5035(13) 0.4017(9) 0.1374(6) 0.046(3) Uiso 1 1 d . . .
H21A H 0.4123 0.3452 0.1157 0.069 Uiso 1 1 calc R . .
H21B H 0.5344 0.3902 0.1799 0.069 Uiso 1 1 calc R . .
H21C H 0.5753 0.4018 0.1095 0.069 Uiso 1 1 calc R . .
C22 C 0.380(3) 0.543(2) 0.0788(14) 0.171(11) Uiso 1 1 d . . .
H22A H 0.3751 0.6124 0.0908 0.257 Uiso 1 1 calc R . .
H22B H 0.2837 0.4886 0.0675 0.257 Uiso 1 1 calc R . .
H22C H 0.4285 0.5374 0.0408 0.257 Uiso 1 1 calc R . .
C23 C 0.6478(9) 0.6423(7) 0.1924(4) 0.0157(19) Uiso 1 1 d . . .
C24 C 0.7827(9) 0.6411(7) 0.2013(4) 0.0157(19) Uiso 1 1 d . . .
H24 H 0.8512 0.7011 0.2321 0.019 Uiso 1 1 calc R . .
C25 C 0.8366(10) 0.5656(7) 0.1724(5) 0.023(2) Uiso 1 1 d D . .
C26 C 0.9076(11) 0.5202(8) 0.2073(5) 0.027(2) Uiso 1 1 d . . .
H26 H 0.9282 0.5455 0.2539 0.033 Uiso 1 1 calc R . .
C27 C 0.9508(14) 0.4426(10) 0.1812(6) 0.049(3) Uiso 1 1 d . . .
H27 H 0.9880 0.4105 0.2104 0.059 Uiso 1 1 calc R . .
C28 C 0.9450(15) 0.4116(11) 0.1235(7) 0.059(4) Uiso 1 1 d D . .
H28 H 0.9834 0.3602 0.1076 0.071 Uiso 1 1 calc R . .
C29 C 0.8725(14) 0.4578(11) 0.0744(7) 0.055(4) Uiso 1 1 d D . .
H29 H 0.8618 0.4335 0.0280 0.066 Uiso 1 1 calc R . .
C30 C 0.8227(14) 0.5394(10) 0.1033(6) 0.048(3) Uiso 1 1 d D . .
H30 H 0.7825 0.5735 0.0767 0.057 Uiso 1 1 calc R . .
C31 C 0.6184(10) 0.7328(8) 0.2286(5) 0.026(2) Uiso 1 1 d D . .
C32 C 0.6384(14) 0.7646(10) 0.3007(6) 0.051(3) Uiso 1 1 d D . .
H32 H 0.6771 0.7269 0.3249 0.061 Uiso 1 1 calc R . .
C33 C 0.6077(12) 0.8395(9) 0.3338(6) 0.041(3) Uiso 1 1 d D . .
H33 H 0.6187 0.8527 0.3804 0.050 Uiso 1 1 calc R . .
C34 C 0.5619(13) 0.8969(11) 0.3035(7) 0.060(4) Uiso 1 1 d D . .
H34 H 0.5411 0.9524 0.3290 0.072 Uiso 1 1 calc R . .
C35 C 0.5411(10) 0.8809(7) 0.2336(4) 0.023(2) Uiso 1 1 d D . .
H35 H 0.5010 0.9210 0.2124 0.027 Uiso 1 1 calc R . .
C36 C 0.5848(10) 0.7988(7) 0.1954(5) 0.024(2) Uiso 1 1 d D . .
C37 C 0.5846(10) 0.7950(7) 0.1244(4) 0.017(2) Uiso 1 1 d . . .
C38 C 0.4588(13) 0.7911(10) 0.0199(6) 0.043(3) Uiso 1 1 d . . .
H38A H 0.3635 0.7873 0.0028 0.065 Uiso 1 1 calc R . .
H38B H 0.4749 0.7298 -0.0045 0.065 Uiso 1 1 calc R . .
H38C H 0.5306 0.8556 0.0145 0.065 Uiso 1 1 calc R . .
N1 N -0.0315(8) -0.2035(6) 0.0915(3) 0.0194(18) Uani 1 1 d . . .
H1 H -0.0919 -0.1886 0.1153 0.023 Uiso 1 1 calc R . .
N2 N 0.4702(9) 0.7918(7) 0.0911(4) 0.032(2) Uani 1 1 d . . .
H2 H 0.3969 0.7901 0.1107 0.038 Uiso 1 1 calc R . .
O1 O 0.1930(7) -0.2052(6) 0.0953(4) 0.041(2) Uani 1 1 d . . .
O2 O 0.6824(7) 0.7801(5) 0.1010(3) 0.0270(17) Uani 1 1 d . . .
Si1 Si 0.1761(3) 0.0872(2) 0.17457(19) 0.0383(7) Uani 1 1 d . . .
Si2 Si 0.4829(3) 0.5217(2) 0.15033(19) 0.0383(7) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 Si1 1.853(12) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 Si1 1.793(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 Si1 1.955(19) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.353(14) . ?
C4 C12 1.553(15) . ?
C4 Si1 1.869(10) . ?
C5 C6 1.470(14) . ?
C5 H5 0.9500 . ?
C6 C11 1.338(16) . ?
C6 C7 1.437(15) . ?
C7 C8 1.532(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.420(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.269(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(17) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.369(14) . ?
C12 C13 1.413(16) . ?
C13 C14 1.38(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.256(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.442(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.414(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.505(13) . ?
C18 O1 1.225(12) . ?
C18 N1 1.351(13) . ?
C19 N1 1.511(12) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 Si2 1.874(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 Si2 1.733(13) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 Si2 1.87(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.370(13) . ?
C23 C31 1.480(13) . ?
C23 Si2 1.898(9) . ?
C24 C25 1.411(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.365(14) . ?
C25 C30 1.407(15) . ?
C26 C27 1.345(16) . ?
C26 H26 0.9500 . ?
C27 C28 1.193(17) . ?
C27 H27 0.9500 . ?
C28 C29 1.57(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.451(18) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.371(14) . ?
C31 C32 1.467(15) . ?
C32 C33 1.287(17) . ?
C32 H32 0.9500 . ?
C33 C34 1.292(18) . ?
C33 H33 0.9500 . ?
C34 C35 1.426(16) . ?
C34 H34 0.9500 . ?
C35 C36 1.488(14) . ?
C35 H35 0.9500 . ?
C36 C37 1.484(13) . ?
C37 O2 1.212(11) . ?
C37 N2 1.280(12) . ?
C38 N2 1.489(14) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C12 114.7(8) . . ?
C5 C4 Si1 127.6(8) . . ?
C12 C4 Si1 117.0(7) . . ?
C4 C5 C6 124.7(9) . . ?
C4 C5 H5 117.7 . . ?
C6 C5 H5 117.7 . . ?
C11 C6 C7 123.9(11) . . ?
C11 C6 C5 121.2(10) . . ?
C7 C6 C5 114.9(9) . . ?
C6 C7 C8 110.9(11) . . ?
C6 C7 H7 124.5 . . ?
C8 C7 H7 124.5 . . ?
C9 C8 C7 116.4(13) . . ?
C9 C8 H8 121.8 . . ?
C7 C8 H8 121.8 . . ?
C10 C9 C8 129.6(14) . . ?
C10 C9 H9 115.2 . . ?
C8 C9 H9 115.2 . . ?
C9 C10 C11 114.0(12) . . ?
C9 C10 H10 123.0 . . ?
C11 C10 H10 123.0 . . ?
C6 C11 C10 124.8(12) . . ?
C6 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
C17 C12 C13 115.1(11) . . ?
C17 C12 C4 125.3(9) . . ?
C13 C12 C4 118.4(10) . . ?
C14 C13 C12 123.0(13) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C15 C14 C13 123.5(15) . . ?
C15 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C14 C15 C16 115.4(13) . . ?
C14 C15 H15 122.3 . . ?
C16 C15 H15 122.3 . . ?
C17 C16 C15 123.6(10) . . ?
C17 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C12 C17 C16 118.1(9) . . ?
C12 C17 C18 124.5(9) . . ?
C16 C17 C18 116.5(8) . . ?
O1 C18 N1 124.7(9) . . ?
O1 C18 C17 117.6(9) . . ?
N1 C18 C17 116.3(8) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si2 C20 H20A 109.5 . . ?
Si2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si2 C21 H21A 109.5 . . ?
Si2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si2 C22 H22A 109.5 . . ?
Si2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C31 120.4(8) . . ?
C24 C23 Si2 123.6(7) . . ?
C31 C23 Si2 114.7(6) . . ?
C23 C24 C25 130.7(8) . . ?
C23 C24 H24 114.6 . . ?
C25 C24 H24 114.6 . . ?
C26 C25 C30 117.8(10) . . ?
C26 C25 C24 124.1(9) . . ?
C30 C25 C24 118.0(10) . . ?
C27 C26 C25 125.4(10) . . ?
C27 C26 H26 117.3 . . ?
C25 C26 H26 117.3 . . ?
C28 C27 C26 123.8(15) . . ?
C28 C27 H27 118.1 . . ?
C26 C27 H27 118.1 . . ?
C27 C28 C29 118.5(15) . . ?
C27 C28 H28 120.8 . . ?
C29 C28 H28 120.8 . . ?
C30 C29 C28 116.9(12) . . ?
C30 C29 H29 121.5 . . ?
C28 C29 H29 121.5 . . ?
C25 C30 C29 117.0(12) . . ?
C25 C30 H30 121.5 . . ?
C29 C30 H30 121.5 . . ?
C36 C31 C32 116.0(10) . . ?
C36 C31 C23 120.2(9) . . ?
C32 C31 C23 123.4(10) . . ?
C33 C32 C31 125.2(13) . . ?
C33 C32 H32 117.4 . . ?
C31 C32 H32 117.4 . . ?
C32 C33 C34 120.0(14) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 123.0(14) . . ?
C33 C34 H34 118.5 . . ?
C35 C34 H34 118.5 . . ?
C34 C35 C36 117.3(10) . . ?
C34 C35 H35 121.4 . . ?
C36 C35 H35 121.4 . . ?
C31 C36 C37 126.3(9) . . ?
C31 C36 C35 117.2(9) . . ?
C37 C36 C35 116.5(9) . . ?
O2 C37 N2 125.0(9) . . ?
O2 C37 C36 117.7(9) . . ?
N2 C37 C36 116.3(9) . . ?
N2 C38 H38A 109.5 . . ?
N2 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N2 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C18 N1 C19 121.7(8) . . ?
C18 N1 H1 119.1 . . ?
C19 N1 H1 119.1 . . ?
C37 N2 C38 121.3(9) . . ?
C37 N2 H2 119.4 . . ?
C38 N2 H2 119.4 . . ?
C2 Si1 C1 109.6(6) . . ?
C2 Si1 C4 106.7(5) . . ?
C1 Si1 C4 112.8(5) . . ?
C2 Si1 C3 105.6(7) . . ?
C1 Si1 C3 107.2(7) . . ?
C4 Si1 C3 114.8(7) . . ?
C21 Si2 C20 113.4(7) . . ?
C21 Si2 C22 115.6(10) . . ?
C20 Si2 C22 90.6(11) . . ?
C21 Si2 C23 116.3(5) . . ?
C20 Si2 C23 105.1(6) . . ?
C22 Si2 C23 112.6(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.640
_refine_diff_density_min         -1.702
_refine_diff_density_rms         0.157
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2087805'
loop_
_audit_author_name
_audit_author_address
'Jen-Chieh Hsieh'
;Tamkang University
Taiwan
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11.50 Br0 N0.50'
_chemical_formula_weight         198.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5913(10)
_cell_length_b                   11.309(2)
_cell_length_c                   16.066(4)
_cell_angle_alpha                69.396(4)
_cell_angle_beta                 84.651(7)
_cell_angle_gamma                88.169(4)
_cell_volume                     1116.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    425
_cell_measurement_theta_min      1.9199
_cell_measurement_theta_max      21.5816

_exptl_crystal_description       acicular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_correction_T_min  0.7106
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 QUEST CMOS PHOTON II four-circle KAPPA diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            91333
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         28.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5569
_reflns_number_gt                4137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.2405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5569
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.23267(17) 0.42400(10) 0.12333(7) 0.0476(3) Uani 1 1 d . . . . .
C1 C 0.3204(2) 0.53801(12) 0.09324(8) 0.0467(3) Uani 1 1 d . . . . .
C2 C 0.45565(19) 0.57402(12) 0.14226(8) 0.0442(3) Uani 1 1 d . . . . .
C3 C 0.49113(18) 0.48939(12) 0.22710(8) 0.0432(3) Uani 1 1 d . . . . .
C4 C 0.39162(19) 0.37179(12) 0.26066(8) 0.0440(3) Uani 1 1 d . . . . .
C5 C 0.26929(19) 0.34176(12) 0.20402(8) 0.0445(3) Uani 1 1 d . . . . .
C6 C 0.2616(2) 0.62492(15) 0.00416(10) 0.0619(4) Uani 1 1 d . . . . .
H6A H 0.371307 0.629959 -0.040663 0.093 Uiso 1 1 calc R U . . .
H6B H 0.233928 0.707524 0.006658 0.093 Uiso 1 1 calc R U . . .
H6C H 0.141940 0.592847 -0.010469 0.093 Uiso 1 1 calc R U . . .
C7 C 0.5496(2) 0.70234(12) 0.10701(8) 0.0465(3) Uani 1 1 d . . . . .
C8 C 0.6941(2) 0.73657(14) 0.03442(10) 0.0570(3) Uani 1 1 d . . . . .
H8 H 0.731702 0.679576 0.005832 0.068 Uiso 1 1 calc R U . . .
C9 C 0.7827(3) 0.85502(16) 0.00418(12) 0.0699(4) Uani 1 1 d . . . . .
H9 H 0.879810 0.877283 -0.044575 0.084 Uiso 1 1 calc R U . . .
C10 C 0.7281(3) 0.93966(16) 0.04564(13) 0.0732(5) Uani 1 1 d . . . . .
H10 H 0.789479 1.018831 0.025576 0.088 Uiso 1 1 calc R U . . .
C11 C 0.5833(3) 0.90786(15) 0.11661(12) 0.0686(4) Uani 1 1 d . . . . .
H11 H 0.544756 0.965869 0.144229 0.082 Uiso 1 1 calc R U . . .
C12 C 0.4943(2) 0.78974(14) 0.14724(10) 0.0566(3) Uani 1 1 d . . . . .
H12 H 0.395936 0.768689 0.195528 0.068 Uiso 1 1 calc R U . . .
C13 C 0.63198(19) 0.52713(12) 0.28105(8) 0.0448(3) Uani 1 1 d . . . . .
C14 C 0.8368(2) 0.54420(14) 0.25284(10) 0.0554(3) Uani 1 1 d . . . . .
H14 H 0.886672 0.530573 0.200880 0.066 Uiso 1 1 calc R U . . .
C15 C 0.9682(2) 0.58138(16) 0.30122(13) 0.0692(4) Uani 1 1 d . . . . .
H15 H 1.106075 0.592286 0.281887 0.083 Uiso 1 1 calc R U . . .
C16 C 0.8956(3) 0.60221(17) 0.37770(12) 0.0735(5) Uani 1 1 d . . . . .
H16 H 0.984278 0.626851 0.410360 0.088 Uiso 1 1 calc R U . . .
C17 C 0.6923(3) 0.58669(17) 0.40594(11) 0.0693(4) Uani 1 1 d . . . . .
H17 H 0.642843 0.601673 0.457452 0.083 Uiso 1 1 calc R U . . .
C18 C 0.5609(2) 0.54883(14) 0.35803(9) 0.0562(3) Uani 1 1 d . . . . .
H18 H 0.423221 0.537845 0.377772 0.067 Uiso 1 1 calc R U . . .
C19 C 0.4047(2) 0.28641(12) 0.35496(8) 0.0476(3) Uani 1 1 d . . . . .
C20 C 0.5884(2) 0.24046(14) 0.38899(10) 0.0599(4) Uani 1 1 d . . . . .
H20 H 0.709108 0.261600 0.352181 0.072 Uiso 1 1 calc R U . . .
C21 C 0.5934(3) 0.16337(17) 0.47731(12) 0.0753(5) Uani 1 1 d . . . . .
H21 H 0.717566 0.132827 0.499457 0.090 Uiso 1 1 calc R U . . .
C22 C 0.4174(3) 0.13169(17) 0.53237(12) 0.0795(5) Uani 1 1 d . . . . .
H22 H 0.422086 0.080324 0.591836 0.095 Uiso 1 1 calc R U . . .
C23 C 0.2344(3) 0.17568(16) 0.49982(10) 0.0702(5) Uani 1 1 d . . . . .
H23 H 0.114396 0.153357 0.537018 0.084 Uiso 1 1 calc R U . . .
C24 C 0.2277(2) 0.25313(14) 0.41186(9) 0.0565(3) Uani 1 1 d . . . . .
H24 H 0.102860 0.283442 0.390427 0.068 Uiso 1 1 calc R U . . .
C25 C 0.1688(2) 0.21667(13) 0.22655(8) 0.0480(3) Uani 1 1 d . . . . .
C26 C 0.2677(3) 0.10343(14) 0.26630(10) 0.0606(4) Uani 1 1 d . . . . .
H26 H 0.398268 0.104174 0.283616 0.073 Uiso 1 1 calc R U . . .
C27 C 0.1740(3) -0.01098(16) 0.28052(12) 0.0737(5) Uani 1 1 d . . . . .
H27 H 0.242289 -0.086334 0.306849 0.088 Uiso 1 1 calc R U . . .
C28 C -0.0192(3) -0.01320(18) 0.25584(12) 0.0776(5) Uani 1 1 d . . . . .
H28 H -0.081630 -0.089901 0.265053 0.093 Uiso 1 1 calc R U . . .
C29 C -0.1197(3) 0.09804(19) 0.21756(12) 0.0731(5) Uani 1 1 d . . . . .
H29 H -0.251333 0.096542 0.201573 0.088 Uiso 1 1 calc R U . . .
C30 C -0.0266(2) 0.21264(15) 0.20250(10) 0.0585(4) Uani 1 1 d . . . . .
H30 H -0.095839 0.287561 0.176014 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3368(16) . ?
N1 C5 1.3413(17) . ?
C1 C2 1.4004(17) . ?
C1 C6 1.5010(19) . ?
C2 C3 1.3983(18) . ?
C2 C7 1.4913(17) . ?
C3 C4 1.4052(17) . ?
C3 C13 1.4937(17) . ?
C4 C5 1.4019(17) . ?
C4 C19 1.4915(18) . ?
C5 C25 1.4920(17) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.382(2) . ?
C7 C8 1.3838(18) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.3805(18) . ?
C13 C18 1.3812(19) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.385(2) . ?
C19 C24 1.3874(19) . ?
C20 C21 1.382(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.385(2) . ?
C25 C26 1.386(2) . ?
C26 C27 1.387(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.372(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.370(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.385(2) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 119.69(11) . . ?
N1 C1 C2 122.08(12) . . ?
N1 C1 C6 115.41(11) . . ?
C2 C1 C6 122.50(12) . . ?
C3 C2 C1 118.31(11) . . ?
C3 C2 C7 120.89(11) . . ?
C1 C2 C7 120.70(11) . . ?
C2 C3 C4 119.69(11) . . ?
C2 C3 C13 119.06(11) . . ?
C4 C3 C13 121.24(11) . . ?
C5 C4 C3 117.44(11) . . ?
C5 C4 C19 121.39(11) . . ?
C3 C4 C19 121.04(11) . . ?
N1 C5 C4 122.56(11) . . ?
N1 C5 C25 113.50(11) . . ?
C4 C5 C25 123.94(12) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.53(13) . . ?
C12 C7 C2 120.13(12) . . ?
C8 C7 C2 121.35(12) . . ?
C9 C8 C7 120.36(14) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.29(15) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.01(14) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.02(15) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.78(14) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 118.78(12) . . ?
C14 C13 C3 119.89(12) . . ?
C18 C13 C3 121.31(12) . . ?
C13 C14 C15 120.51(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.09(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.93(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.10(15) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.58(14) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 C24 118.20(13) . . ?
C20 C19 C4 122.43(13) . . ?
C24 C19 C4 119.36(12) . . ?
C21 C20 C19 120.42(16) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.52(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.89(16) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.06(17) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.90(15) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C30 C25 C26 118.39(13) . . ?
C30 C25 C5 119.06(13) . . ?
C26 C25 C5 122.45(13) . . ?
C25 C26 C27 120.70(16) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 120.14(18) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 119.74(15) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.47(17) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.56(16) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d23248
_database_code_depnum_ccdc_archive 'CCDC 2087803'
loop_
_audit_author_name
_audit_author_address
'Jen-Chieh Hsieh'
;Tamkang University
Taiwan
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N O Si'
_chemical_formula_sum            'C19 H21 N O Si'
_chemical_formula_weight         307.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9558(3)
_cell_length_b                   9.7312(4)
_cell_length_c                   10.0870(4)
_cell_angle_alpha                102.940(2)
_cell_angle_beta                 96.5450(10)
_cell_angle_gamma                103.5060(10)
_cell_volume                     820.15(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6582
_cell_measurement_theta_min      2.639
_cell_measurement_theta_max      25.078

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9080
_exptl_absorpt_correction_T_max  0.9444
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11110
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2884
_reflns_number_gt                2609
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.5958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2884
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.676
_refine_ls_shift/su_mean         0.010

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5631(3) 0.4046(4) 0.1189(3) 0.0586(8) Uani 1 1 d . . .
H1A H 0.6464 0.4385 0.0692 0.088 Uiso 1 1 calc R . .
H1B H 0.5277 0.4880 0.1651 0.088 Uiso 1 1 calc R . .
H1C H 0.4756 0.3326 0.0534 0.088 Uiso 1 1 calc R . .
C2 C 0.7029(3) 0.1598(3) 0.1569(3) 0.0453(6) Uani 1 1 d . . .
H2A H 0.6161 0.0930 0.0867 0.068 Uiso 1 1 calc R . .
H2B H 0.7361 0.1081 0.2229 0.068 Uiso 1 1 calc R . .
H2C H 0.7904 0.1952 0.1121 0.068 Uiso 1 1 calc R . .
C3 C 0.8106(3) 0.4666(3) 0.3592(3) 0.0409(5) Uani 1 1 d . . .
H3A H 0.8689 0.5173 0.2997 0.061 Uiso 1 1 calc R . .
H3B H 0.8785 0.4231 0.4101 0.061 Uiso 1 1 calc R . .
H3C H 0.7741 0.5367 0.4247 0.061 Uiso 1 1 calc R . .
C4 C 0.4990(2) 0.2525(2) 0.36528(19) 0.0233(4) Uani 1 1 d . . .
C5 C 0.5612(2) 0.2189(2) 0.49153(19) 0.0241(4) Uani 1 1 d . . .
C6 C 0.7170(2) 0.2135(2) 0.5223(2) 0.0322(5) Uani 1 1 d . . .
H6 H 0.7841 0.2286 0.4574 0.039 Uiso 1 1 calc R . .
C7 C 0.7745(3) 0.1871(2) 0.6441(2) 0.0382(5) Uani 1 1 d . . .
H7 H 0.8796 0.1828 0.6614 0.046 Uiso 1 1 calc R . .
C8 C 0.6795(3) 0.1666(3) 0.7417(2) 0.0408(6) Uani 1 1 d . . .
H8 H 0.7204 0.1527 0.8273 0.049 Uiso 1 1 calc R . .
C9 C 0.5259(3) 0.1666(2) 0.7131(2) 0.0371(5) Uani 1 1 d . . .
H9 H 0.4600 0.1506 0.7787 0.044 Uiso 1 1 calc R . .
C10 C 0.4652(2) 0.1898(2) 0.5882(2) 0.0277(4) Uani 1 1 d . . .
C11 C 0.2985(2) 0.1763(2) 0.5585(2) 0.0295(5) Uani 1 1 d . . .
C12 C 0.0742(2) 0.1636(3) 0.3941(2) 0.0362(5) Uani 1 1 d . . .
H12A H 0.0426 0.1243 0.2938 0.054 Uiso 1 1 calc R . .
H12B H 0.0430 0.2543 0.4232 0.054 Uiso 1 1 calc R . .
H12C H 0.0234 0.0919 0.4405 0.054 Uiso 1 1 calc R . .
C13 C 0.3424(2) 0.2374(2) 0.34046(19) 0.0233(4) Uani 1 1 d . . .
C14 C 0.2605(2) 0.2632(2) 0.21446(19) 0.0244(4) Uani 1 1 d . . .
C15 C 0.2220(3) 0.3949(2) 0.2196(2) 0.0329(5) Uani 1 1 d . . .
H15 H 0.2464 0.4688 0.3042 0.039 Uiso 1 1 calc R . .
C16 C 0.1482(3) 0.4178(3) 0.1015(2) 0.0400(5) Uani 1 1 d . . .
H16 H 0.1223 0.5077 0.1055 0.048 Uiso 1 1 calc R . .
C17 C 0.1122(3) 0.3116(3) -0.0217(2) 0.0417(6) Uani 1 1 d . . .
H17 H 0.0624 0.3286 -0.1024 0.050 Uiso 1 1 calc R . .
C18 C 0.1484(3) 0.1808(3) -0.0277(2) 0.0447(6) Uani 1 1 d . . .
H18 H 0.1234 0.1072 -0.1126 0.054 Uiso 1 1 calc R . .
C19 C 0.2216(3) 0.1564(2) 0.0905(2) 0.0365(5) Uani 1 1 d . . .
H19 H 0.2451 0.0654 0.0862 0.044 Uiso 1 1 calc R . .
N1 N 0.24414(19) 0.19424(18) 0.43115(17) 0.0267(4) Uani 1 1 d . . .
O1 O 0.20772(19) 0.1467(2) 0.63709(16) 0.0452(4) Uani 1 1 d . . .
Si1 Si 0.63850(6) 0.31869(6) 0.25008(5) 0.02704(19) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 Si1 1.860(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 Si1 1.870(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 Si1 1.878(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C13 1.364(3) . ?
C4 C5 1.466(3) . ?
C4 Si1 1.9014(19) . ?
C5 C10 1.404(3) . ?
C5 C6 1.411(3) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.457(3) . ?
C11 O1 1.230(3) . ?
C11 N1 1.384(3) . ?
C12 N1 1.468(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.404(3) . ?
C13 C14 1.494(3) . ?
C14 C19 1.384(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C13 C4 C5 116.63(17) . . ?
C13 C4 Si1 124.14(14) . . ?
C5 C4 Si1 119.20(14) . . ?
C10 C5 C6 116.83(18) . . ?
C10 C5 C4 120.43(18) . . ?
C6 C5 C4 122.74(18) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 120.8(2) . . ?
C5 C10 C11 120.84(18) . . ?
C9 C10 C11 118.28(19) . . ?
O1 C11 N1 120.42(19) . . ?
O1 C11 C10 123.9(2) . . ?
N1 C11 C10 115.67(17) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 N1 122.47(17) . . ?
C4 C13 C14 123.16(17) . . ?
N1 C13 C14 114.37(16) . . ?
C19 C14 C15 118.85(19) . . ?
C19 C14 C13 120.42(18) . . ?
C15 C14 C13 120.73(17) . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C11 N1 C13 123.31(16) . . ?
C11 N1 C12 115.76(16) . . ?
C13 N1 C12 120.93(17) . . ?
C1 Si1 C2 107.77(14) . . ?
C1 Si1 C3 103.73(13) . . ?
C2 Si1 C3 110.53(11) . . ?
C1 Si1 C4 116.84(10) . . ?
C2 Si1 C4 108.48(10) . . ?
C3 Si1 C4 109.37(10) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.046
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2087801'
loop_
_audit_author_name
_audit_author_address
'Jen-Chieh Hsieh'
;Tamkang University
Taiwan
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Br0 N O'
_chemical_formula_weight         313.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0738(5)
_cell_length_b                   8.9358(4)
_cell_length_c                   14.7988(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.019(2)
_cell_angle_gamma                90
_cell_volume                     1727.79(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40164
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4266
_reflns_number_gt                2321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.6305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4266
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1618
_refine_ls_R_factor_gt           0.0828
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18216(14) -0.05744(18) 0.29651(12) 0.0631(5) Uani 1 1 d . . . . .
N1 N 0.28001(14) 0.1366(2) 0.25625(12) 0.0485(5) Uani 1 1 d . . . . .
H1 H 0.282414 0.220517 0.227982 0.058 Uiso 1 1 d R U . . .
C1 C 0.02458(19) 0.1801(3) 0.25363(19) 0.0609(7) Uani 1 1 d . . . . .
H1A H 0.026514 0.161948 0.315545 0.073 Uiso 1 1 calc R U . . .
C2 C -0.0575(2) 0.2559(3) 0.2148(2) 0.0718(8) Uani 1 1 d . . . . .
H2A H -0.109752 0.290372 0.250429 0.086 Uiso 1 1 calc R U . . .
C3 C -0.0619(2) 0.2799(3) 0.1236(2) 0.0748(9) Uani 1 1 d . . . . .
H3 H -0.117069 0.331267 0.097098 0.090 Uiso 1 1 calc R U . . .
C4 C 0.01529(19) 0.2283(3) 0.07085(19) 0.0631(7) Uani 1 1 d . . . . .
H4 H 0.010697 0.244619 0.008766 0.076 Uiso 1 1 calc R U . . .
C5 C 0.10044(17) 0.1521(2) 0.10778(16) 0.0462(6) Uani 1 1 d . . . . .
C6 C 0.10488(17) 0.1303(2) 0.20182(15) 0.0446(6) Uani 1 1 d . . . . .
C7 C 0.19261(18) 0.0603(3) 0.25368(15) 0.0451(6) Uani 1 1 d . . . . .
C8 C 0.3710(2) 0.0845(3) 0.30492(19) 0.0682(8) Uani 1 1 d . . . . .
H8A H 0.423907 0.158536 0.301498 0.102 Uiso 1 1 calc R U . . .
H8B H 0.393746 -0.007288 0.278490 0.102 Uiso 1 1 calc R U . . .
H8C H 0.355778 0.067514 0.367075 0.102 Uiso 1 1 calc R U . . .
C9 C 0.17825(16) 0.0958(2) 0.04477(15) 0.0437(5) Uani 1 1 d . . . . .
C10 C 0.22916(17) -0.0322(3) 0.05961(15) 0.0454(6) Uani 1 1 d . . . . .
H10 H 0.209651 -0.085198 0.110268 0.055 Uiso 1 1 calc R U . . .
C11 C 0.31111(17) -0.1029(3) 0.00876(14) 0.0450(6) Uani 1 1 d . . . . .
C12 C 0.3341(2) -0.2517(3) 0.02650(18) 0.0635(7) Uani 1 1 d . . . . .
H12 H 0.295133 -0.303947 0.067336 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4128(2) -0.3244(3) -0.0144(2) 0.0767(9) Uani 1 1 d . . . . .
H13 H 0.426233 -0.424309 -0.000997 0.092 Uiso 1 1 calc R U . . .
C14 C 0.4715(2) -0.2504(4) -0.07485(19) 0.0711(9) Uani 1 1 d . . . . .
H14 H 0.524859 -0.299209 -0.102592 0.085 Uiso 1 1 calc R U . . .
C15 C 0.4504(2) -0.1036(4) -0.09372(17) 0.0677(8) Uani 1 1 d . . . . .
H15 H 0.489677 -0.052711 -0.134982 0.081 Uiso 1 1 calc R U . . .
C16 C 0.37198(19) -0.0297(3) -0.05261(16) 0.0571(7) Uani 1 1 d . . . . .
H16 H 0.359577 0.070427 -0.066104 0.069 Uiso 1 1 calc R U . . .
C17 C 0.18849(17) 0.1853(3) -0.03981(15) 0.0450(6) Uani 1 1 d . . . . .
C18 C 0.23450(19) 0.3245(3) -0.03903(17) 0.0555(6) Uani 1 1 d . . . . .
H18 H 0.260662 0.364531 0.015002 0.067 Uiso 1 1 calc R U . . .
C19 C 0.2417(2) 0.4045(3) -0.1188(2) 0.0686(8) Uani 1 1 d . . . . .
H19 H 0.273786 0.497345 -0.118082 0.082 Uiso 1 1 calc R U . . .
C20 C 0.2022(2) 0.3485(4) -0.1983(2) 0.0727(9) Uani 1 1 d . . . . .
H20 H 0.207226 0.403233 -0.251421 0.087 Uiso 1 1 calc R U . . .
C21 C 0.1551(2) 0.2119(4) -0.19984(18) 0.0736(8) Uani 1 1 d . . . . .
H21 H 0.127256 0.174440 -0.253914 0.088 Uiso 1 1 calc R U . . .
C22 C 0.1488(2) 0.1291(3) -0.12093(17) 0.0603(7) Uani 1 1 d . . . . .
H22 H 0.117776 0.035378 -0.122506 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.239(3) . ?
N1 C7 1.330(3) . ?
N1 C8 1.446(3) . ?
N1 H1 0.8601 . ?
C1 C2 1.378(4) . ?
C1 C6 1.395(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.365(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(3) . ?
C5 C9 1.491(3) . ?
C6 C7 1.494(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.338(3) . ?
C9 C17 1.496(3) . ?
C10 C11 1.473(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 C22 1.386(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 122.7(2) . . ?
C7 N1 H1 118.6 . . ?
C8 N1 H1 118.7 . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 H1A 119.4 . . ?
C6 C1 H1A 119.4 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 C9 118.1(2) . . ?
C6 C5 C9 124.6(2) . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 C7 115.5(2) . . ?
C5 C6 C7 124.84(19) . . ?
O1 C7 N1 122.1(2) . . ?
O1 C7 C6 121.4(2) . . ?
N1 C7 C6 116.3(2) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C5 122.2(2) . . ?
C10 C9 C17 122.4(2) . . ?
C5 C9 C17 115.20(19) . . ?
C9 C10 C11 130.5(2) . . ?
C9 C10 H10 114.7 . . ?
C11 C10 H10 114.7 . . ?
C12 C11 C16 116.7(2) . . ?
C12 C11 C10 118.1(2) . . ?
C16 C11 C10 125.1(2) . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C18 C17 C22 118.9(2) . . ?
C18 C17 C9 121.8(2) . . ?
C22 C17 C9 119.3(2) . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.2(3) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.5(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 C9 177.9(2) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
C2 C1 C6 C7 175.5(2) . . . . ?
C4 C5 C6 C1 1.9(3) . . . . ?
C9 C5 C6 C1 -176.1(2) . . . . ?
C4 C5 C6 C7 -175.9(2) . . . . ?
C9 C5 C6 C7 6.1(4) . . . . ?
C8 N1 C7 O1 3.4(3) . . . . ?
C8 N1 C7 C6 179.0(2) . . . . ?
C1 C6 C7 O1 64.4(3) . . . . ?
C5 C6 C7 O1 -117.7(3) . . . . ?
C1 C6 C7 N1 -111.2(2) . . . . ?
C5 C6 C7 N1 66.7(3) . . . . ?
C4 C5 C9 C10 -145.3(2) . . . . ?
C6 C5 C9 C10 32.7(3) . . . . ?
C4 C5 C9 C17 29.6(3) . . . . ?
C6 C5 C9 C17 -152.4(2) . . . . ?
C5 C9 C10 C11 -176.8(2) . . . . ?
C17 C9 C10 C11 8.7(4) . . . . ?
C9 C10 C11 C12 -165.2(2) . . . . ?
C9 C10 C11 C16 18.6(4) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?
C10 C11 C12 C13 -176.7(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C12 C11 C16 C15 0.5(4) . . . . ?
C10 C11 C16 C15 176.7(2) . . . . ?
C10 C9 C17 C18 -112.3(3) . . . . ?
C5 C9 C17 C18 72.8(3) . . . . ?
C10 C9 C17 C22 69.2(3) . . . . ?
C5 C9 C17 C22 -105.7(2) . . . . ?
C22 C17 C18 C19 -0.9(4) . . . . ?
C9 C17 C18 C19 -179.4(2) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C18 C17 C22 C21 -0.2(4) . . . . ?
C9 C17 C22 C21 178.3(2) . . . . ?
C20 C21 C22 C17 1.1(4) . . . . ?

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037

